Hydrochloric Acid → HCID 18673079, compound

HRID 1058098Notes

Reaction equation

HRID 1058098 reaction equation
[NH2:1][C:2]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[CH:3][C:4]([O:6][CH3:7])=[O:5].[ClH:14]>[Pd].C(O)(=O)C>[ClH:14].[ClH:14].[NH2:1][CH:2]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[CH2:3][C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69944552Methyl 3-amino-3-(pyridin-3-YL)prop-2-enoate

Product 1

HCID 18673079HCID 18673079, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
2.5 °C

Procedure

Dry palladium on charcoal (0.54 g, manufactured by Degussa, 5% Pd/C) was added to a solution of methyl 3-Amino-3-(3-pyridyl)-2-propenoate (5.4 g, 30 mmol) in dry acetic acid (13 g) in a 450 ml Pyrex high-pressure bottle. The reaction mixture was hydrogenated at 3-3.2 bar. After 1.5-2 h, the catalyst was filtered and washed with 20 g of isopropyl alcohol until the wash solvent was no longer yellow. Gaseous HCl (10.6 g, 0.3 mol) was bubbled through the stirred filtrate at 5-15° C. The suspension was cooled to 0-5° C. and stirred for two hours. The resulting white precipitate was filtered, washed with 5 g of isopropyl alcohol, and dried at 45° C. to yield 5.95 g (78.4%,) of methyl 3-Amino-3-(3-pyridyl)propanoate dihydrochloride.

Workup

  1. filtrationthe catalyst was filtered
  2. washwashed with 20 g of isopropyl alcohol until the wash solvent
  3. filtrationThe resulting white precipitate was filtered
  4. washwashed with 5 g of isopropyl alcohol
  5. customdried at 45° C.

Sources & evidence

ORD record
ord-26b85370d0f741e5ac26b501527d350c
Source dataset
uspto-grants-2003_02
Patent number
US06515130B1

Reaction notes

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